[Hiring] Director, Security & Infrastructure @Workleap - en

Role Description

As Director, Security & Infrastructure, your role is to create the conditions for product and engineering teams to move faster with confidence. You will lead the infrastructure, security operations, and governance, risk, and compliance functions across Workleap and ShareGate, ensuring our environment remains reliable, scalable, and secure as the organization evolves.

You will play a key role in supporting Workleap’s shift toward a Full-Stack Builder model, where small teams own the full journey from insight to production. This means building a platform and security foundation that reduces friction, strengthens trust, and helps teams ship quickly without compromising reliability, security, or compliance.

Responsibilities:

• Improve platform reliability and scalability so product teams can ship with confidence across Workleap and ShareGate;
• Reduce security and compliance risk through guardrails embedded directly into delivery workflows;
• Increase engineering autonomy by reducing dependency on centralized infrastructure support;
• Increase system resilience and minimize service disruption through stronger observability, incident response, and proactive capacity planning;
• Elevate team impact and organizational leverage by building a high-performing infrastructure and security function;
• Improve executive decision-making with clear, business-relevant visibility into security, compliance, and risk posture.

You will lead a platform-focused team spanning infrastructure, security operations, and GRC, supporting both Workleap and ShareGate. This team is evolving from a traditional support function into a platform enablement team, one that helps product teams move faster by providing reliable, secure, and easy-to-use foundations.

Your role is to position this team as a force multiplier for engineering: reducing friction, increasing autonomy, and making security and infrastructure feel invisible to builder teams.

Your mandate is clear: transform infrastructure and security into silent foundations, robust in the shadows, transparent in everyday use, so that product delivery is smooth and the entire company stands on solid ground.

Next Challenges:

• Enable true self-service so teams can build, deploy, and scale independently;
• Embed security directly into delivery workflows, eliminating manual gates;
• Strengthen platform reliability to support faster and more frequent releases;
• Shift governance from static control to continuous, automated assurance.

Beyond the systems, the real challenge is cultural: turning infrastructure and security into enablers of speed, not constraints. Success means product teams can ship faster with confidence and never have to slow down for infrastructure or security.

Qualifications

• 8+ years of experience across infrastructure and security leadership in technology organizations;
• Experience leading technical teams through transformation in fast-paced, evolving organizations;
• Strong expertise in cloud-native environments such as Azure, AWS, or GCP;
• Hands-on experience with Kubernetes, infrastructure as code, and platform automation;
• Deep understanding of security frameworks, such as SOC 2, NIST CSF, ISO 27001, and CIS Controls;
• Proven ability to build secure, scalable, high-availability environments for SaaS products;
• Strong ability to communicate risk, priorities, and tradeoffs to executive and board-level stakeholders;
• CISSP, CISM, or equivalent credentials are considered an asset;
• Based in Montreal, or able to travel there a few times per quarter.

Benefits

• At Workleap, we build together, we trust each other, and we support each other in success or failure.
• You will be able to express yourself, evolve and develop your creativity in an environment that will adapt to your daily life and your needs.
• We strive to create a healthy and inclusive work environment. This is everyone’s business.

Company Description

Workleap is a Montreal-based tech company on a mission to make work simpler. Since 2006, we’ve been building game-changing products that tackle HR and IT’s biggest challenges. Workleap operates two distinct product lines:

• The Workleap Platform, an AI-powered HR solution designed to drive team performance and boost employee engagement.
• ShareGate, the leading Microsoft 365 migration and governance solution, trusted by IT professionals worldwide for its unmatched simplicity.

Today, more than 20,000 companies rely on Workleap products to grow, lead, and operate with confidence. We’re builders at heart, with a clear purpose: to craft the simplest products that deliver exceptional value for our customers. Period.